SAN JOSE — With the November election leading to a turnover of nearly half the San Jose City Council next year, the stakes are high for Mayor Sam Liccardo as he struggles to maintain allies and secure a majority on a business-friendly council.

The five even-numbered seats on the 10-member City Council are up for election this year. Two of those races were decided in June. Manh Nguyen, who often votes with Liccardo, lost his District 4 seat to challenger Lan Diep, whose likelihood of lining up with Liccardo’s agenda is unclear. Liccardo ally Johnny Khamis kept his District 10 seat.

Term limits will bring new faces to the three remaining seats in Districts 2, 6 and 8. Liccardo loses a longtime adversary when Ash Kalra leaves his District 2 seat. But he also loses two reliable votes with the departures of Pierluigi Oliverio in District 6 and Vice Mayor Rose Herrera in District 8.

“There is no question that a new council makeup could shift power to the left,” said Larry Gerston, professor emeritus of political science at San Jose State. “It would be a fresh breath of air for the labor folks, who have found themselves on the outside looking in for 10 years or so.”

In the election in District 2, which covers the mostly suburban Edenvale and Santa Teresa neighborhoods, Steve Brown, a business-backed security company owner who started a San Jose nonprofit called Meet the Challenge to feed the homeless, is facing off against Sergio Jimenez, a labor-backed investigator at the Santa Clara County Public Defender’s Office.

Brown, who is endorsed by Khamis, former Mayor Chuck Reed and former Councilman Forrest Williams, says he’ll focus on bolstering public safety, improving roads and creating jobs. Brown has come under fire for supporting legislation to prohibit discrimination against businesses because of their “belief that marriage is only a union of one man and one woman,” though he denies accusations of bigotry.

Jimenez, who won support from Kalra, Congresswoman Zoe Lofgren and state Sen. Jim Beall, said his top priorities will be public safety, tackling the housing crisis and improving the city’s quality of life. He’s drawn scrutiny for a bankruptcy and a 20-year-old public drunkenness arrest.

Liccardo hasn’t endorsed in the District 2 race, but the outcome may not win him a friendly vote either way.

Kalra was often on opposite sides of Liccardo, and Jimenez will likely lean in the same direction. Brown, a conservative, could spar with the mayor over issues like new taxes and rent control.

In the race in District 6, which covers Willow Glen and the Rose Garden, Liccardo is counting on a win from business-backed Devora “Dev” Davis, whom he’s endorsed over her opponent, Helen Chapman.

Chapman, a community volunteer with endorsements from organized labor, Lofgren and county Supervisors Dave Cortese and Cindy Chavez, places a focus on bolstering public safety, increasing affordable housing and improving the environment. Chapman faced criticism over alleged mismanagement of funds in new attack ads funded by the San Jose Silicon Valley Chamber of Commerce PAC when she chaired the city’s Parks and Recreation Commission.

Chapman called it “disheartening” and said the “hit piece” was filled with lies. The ads are based on a 2006 audit of the city’s Park Trust Fund, which contains fees that housing developers pay to create parks instead of donating land for parks. The audit found sloppy record-keeping, such as failing to track which developers the money came from, but no evidence that money was misspent or missing.

Davis, an education researcher and businesswoman who’s backed by Liccardo, Reed and Herrera, says she’ll focus on improving public safety, strengthening neighborhoods and bringing more jobs to San Jose. Critics have tried to associate Davis, a Republican, with GOP presidential candidate Donald Trump, though Davis has publicly denounced him.

In District 8, which covers Evergreen and Silver Creek, Evergreen School District board member Sylvia Arenas is running against real estate lawyer Jimmy Nguyen, who’s making his second bid for the seat. Liccardo hasn’t endorsed in the race.

Arenas is backed by organized labor as well as Councilwoman Magdalena Carrasco and her ex, Senate President Pro Tempore Kevin de León. She said her top priorities are public safety, traffic safety and providing quality city services. Arenas has been criticized for accepting financial support from powerful Sacramento politicians.

Nguyen, who was Herrera’s re-election rival, has since garnered her support, along with that of Reed and two current Vietnamese-American council members — Tam Nguyen and outgoing Manh Nguyen. He says he’ll focus on increasing public safety, strengthening the local economy and improving traffic enforcement.

Arenas backers accused Nguyen of switching political camps — from labor to business — after he lost to Herrera four years ago. If he wins, Nguyen is considered more likely to side with the mayor than Arenas.

Liccardo’s council majority seems to shift and change with every major issue — but he could generally rely on favorable votes from Khamis and Councilman Chappie Jones.

But since Liccardo can’t consistently count on support from Carrasco or Tam Nguyen, both of whom opposed the mayor on critical issues such as commercial impact fees and homeless housing, the outcome of the November election is critical for the first-term mayor. Liccardo must win all three seats to maintain a strong majority, and two to maintain the support he has now.

City Council, District 2

Steve Brown

Age: 40

Education: San Jose Police Academy graduate.

Occupation: Businessman/nonprofit chairman.

Family: Married with two children.

Top three priorities: Improve public safety; rebuild roads; create jobs.

Quote: “I’m not a politician, but I am a small-business owner, security expert and community leader whose commitment and experience can help solve some of San Jose’s most pressing problems.”

Sergio A. Jimenez

Age: 39

Education: B.A. in political science from San Jose State; currently in master’s of public administration program at San Jose State.

Occupation: Investigator with Santa Clara County Public Defender’s Office.

Family: Married with three children.

Top three priorities: Safety, housing and quality of life.

Quote: “Our children will be able to achieve their dreams and our future will be safe and sustainable through the work we do today; nothing is more prescient than re-building our safety departments and protecting Coyote Valley.”

Top three priorities: Public safety, affordable housing and environment.

Quote: “I have a deep passion and commitment to community service that extends over 25 years in San Jose. I want to bring that experience to the council working with the community on a variety of levels to benefit all of District 6 neighborhoods and residents.”

Devora “Dev” Joan Davis

Age: 38

Education: Master’s of public policy and master’s of education, Stanford University.

Occupation: Education researcher/businesswoman

Family: Married with a daughter and a son.

Top three priorities: Improving public safety, strengthening neighborhoods and bringing more jobs to San Jose.

Quote: My mother always said, “If you don’t like what’s happening in the world, go out and try to change it.'”

City Council, District 8:

Jimmy Nguyen

Age: 39

Education: Bachelor’s degree in criminology, law and society, psychology and social behavior from UC Irvine. Law degree from University of La Verne College of Law.

Occupation: Attorney.

Family: Single.

Top three priorities: Increase public safety, strengthen local economy, improve traffic enforcement.

Quote: “When you drink from the well, remember the ones who built it.”

Sylvia Arenas

Age: 42

Education: Bachelor’s degree in human development and early childhood development from Cal State East Bay. Master’s degree in public administration from University of San Francisco.

Occupation: Early childhood development specialist

Family: Married with two children, a boy and girl.

Top three priorities: Public safety, traffic safety, providing quality city services for residents.

Quote: “I’m running for City Council to ensure that hard-working families, including my own, can raise thriving children in our community. I support a future for our community that includes safe neighborhoods, abundant parks, open space, local jobs and quality education.”

Ramona Giwargis is the San Jose City Hall reporter at The Mercury News. After stints in Eureka, Salinas and Merced, Giwargis returned to San Jose to cover local government and politics for her hometown newspaper. Giwargis won numerous awards for investigative journalism and is a graduate of San Jose State University.

Otto Warmbier was arrested in January 2016 at the end of a brief tourist visit to North Korea. He had been medically evacuated and was being treated at the University of Cincinnati Medical Center when he died at age 22.